ES2664381T3 - Self-healing polyurethane polymers - Google Patents
Self-healing polyurethane polymers Download PDFInfo
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- ES2664381T3 ES2664381T3 ES15171511.7T ES15171511T ES2664381T3 ES 2664381 T3 ES2664381 T3 ES 2664381T3 ES 15171511 T ES15171511 T ES 15171511T ES 2664381 T3 ES2664381 T3 ES 2664381T3
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/44—Polycarbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4202—Two or more polyesters of different physical or chemical nature
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
- C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6633—Compounds of group C08G18/42
- C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/664—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
Abstract
Uso de un poliuretano, que se puede obtener haciendo reaccionar una mezcla que comprende un isocianato, y: (a) un policarbonato diol y un poliéster diol, o (b) un copolímero de un policarbonato diol y un poliéster diol; como un polímero autorreparable, donde el policarbonato diol es un diol que contiene grupos carbonato y grupos alquileno acíclicos o cíclicos lineales o ramificados que tienen de 2 a 20 átomos de carbono y donde el polímero autorreparable se define como un material polimérico cuya resistencia en tracción después de ser cortado en dos por la mitad, dando como resultado dos mitades y poniéndose en contacto las dos mitades en los cinco minutos posteriores al corte sin un agente de reparación secuestrado, durante 24 horas a una temperatura de 25 °C, es al menos 45 % de la resistencia en tracción de un material polimérico idéntico que no se ha cortado por la mitad, con la condición de que el material polimérico se corte y se mida de acuerdo con la norma ISO 37 usando probetas de pesa tipo 2.Use of a polyurethane, which can be obtained by reacting a mixture comprising an isocyanate, and: (a) a polycarbonate diol and a polyester diol, or (b) a copolymer of a polycarbonate diol and a polyester diol; as a self-healing polymer, where the polycarbonate diol is a diol containing linear or branched acyclic or cyclic alkylene groups and carbonates having 2 to 20 carbon atoms and where the self-healing polymer is defined as a polymeric material whose tensile strength is then of being cut in two in half, resulting in two halves and contacting the two halves in the five minutes after the cut without a sequestered repair agent, for 24 hours at a temperature of 25 ° C, is at least 45 % of the tensile strength of an identical polymeric material that has not been cut in half, with the proviso that the polymeric material is cut and measured in accordance with ISO 37 using type 2 weight specimens.
Description
La curva esfuerzo-deformación (Figura 5) muestra el mismo comportamiento mecánico de los poliuretanos después de la reparación tanto al aire libre como sumergidos en agua; ambas muestras presentan el límite elástico del material virgen, alcanzando el mismo valor de resistencia en tracción en el punto de fluencia. La Tabla 3 muestra los valores de la resistencia en tracción y el porcentaje de eficacia de la reparación, que es casi del 100 %. The stress-strain curve (Figure 5) shows the same mechanical behavior of polyurethanes after repair both outdoors and submerged in water; Both samples have the elastic limit of the virgin material, reaching the same tensile strength value at the creep point. Table 3 shows the tensile strength values and the percentage of repair efficiency, which is almost 100%.
Tabla 3 -Propiedades mecánicas obtenidas a partir de las curvas de esfuerzo-deformación del elastómero de poliuretano preparado de acuerdo con este Ejemplo antes y después de cortar y volver a unir en agua. Table 3 - Mechanical properties obtained from the stress-strain curves of the polyurethane elastomer prepared in accordance with this Example before and after cutting and rejoining in water.
- Resistencia en tracción (virgen) = Tensile strength (virgin) =
- 0,476 MPa 0.476 MPa
- Resistencia en tracción (reparado en agua) = Tensile strength (water repaired) =
- 0,469 MPa 0.469 MPa
- Eficiencia de reparación (24 horas, 25 °C) = Repair efficiency (24 hours, 25 ° C) =
- 98,5 % 98.5%
10 Se obtuvo un elastómero de poliuretano haciendo reaccionar un poliisocianato (Suprasec® 2445 comercial, Huntsman), policaprolactona diol (Pm = 2000 Da) (Sigma Aldrich, Barcelona, España), y 1,4-butanodiol (Sigma Aldrich, Barcelona, España) como un extensor de cadena. Se utilizó una relación NCO/OH de 1,1. 10 A polyurethane elastomer was obtained by reacting a polyisocyanate (Commercial Suprasec® 2445, Huntsman), polycaprolactone diol (Pm = 2000 Da) (Sigma Aldrich, Barcelona, Spain), and 1,4-butanediol (Sigma Aldrich, Barcelona, Spain ) as a chain extender. An NCO / OH ratio of 1.1 was used.
15 Las propiedades mecánicas del poliuretano se midieron mediante una prueba de esfuerzo-deformación en una máquina de ensayo Instron 4411 Universal aplicándola a diferentes muestras de poliuretano troqueladas en forma de campana de descarga tipo 2 de acuerdo con la norma ISO 37. La velocidad de tracción fue de 50 mm/min. 15 The mechanical properties of the polyurethane were measured by a stress-strain test in an Instron 4411 Universal test machine by applying it to different samples of die-cut polyurethane in the form of a type 2 discharge bell according to ISO 37. The traction speed It was 50 mm / min.
La autorreparación del elastómero de poliuretano se probó cortando la muestra de prueba con forma de pesa por la The self-repair of the polyurethane elastomer was tested by cutting the test sample in the form of a weight by
20 mitad y volviendo a unir las dos piezas recién cortadas inmediatamente después del corte, en el sitio del corte, y dejándola a 40 °C durante 24 horas Posteriormente, se repitió la prueba de esfuerzo-deformación y se compararon las propiedades mecánicas. 20 half and re-joining the two freshly cut pieces immediately after cutting, at the cutting site, and leaving it at 40 ° C for 24 hours. Subsequently, the stress-strain test was repeated and the mechanical properties were compared.
La Figura 6 muestra el poliuretano con el corte por la mitad después de volver a unir, antes y después de la prueba Figure 6 shows the polyurethane with the cut in half after reassembly, before and after the test
25 de esfuerzo-deformación. Después de la prueba de esfuerzo-deformación, el poliuretano no se alargó y se rompió en el mismo lugar donde se produjo el corte. Cuando se usa policaprolactona como poliol, no hay autorreparación del material de poliuretano. 25 stress-strain. After the stress-strain test, the polyurethane did not lengthen and broke in the same place where the cut occurred. When polycaprolactone is used as a polyol, there is no self-repair of the polyurethane material.
La Figura 7 compara las curvas de tensión-deformación del material de poliuretano antes y después de que se Figure 7 compares the stress-strain curves of the polyurethane material before and after it is
30 produjo el corte. El límite elástico, la resistencia en tracción y el alargamiento a la rotura del poliuretano antes y después del corte se comparan en la Tabla 4. Después de que se produjo el corte, el poliuretano se rompió justo después del comienzo de la prueba de esfuerzo-deformación. Por lo tanto, no hay autorreparación del poliuretano preparado con policaprolactona como el poliol. 30 produced the cut. The elastic limit, tensile strength and elongation at breakage of the polyurethane before and after the cut are compared in Table 4. After the cut occurred, the polyurethane broke just after the beginning of the stress test. deformation. Therefore, there is no self-repair of polyurethane prepared with polycaprolactone such as polyol.
35 Tabla 4 -Propiedades mecánicas obtenidas de las curvas de esfuerzo-deformación del poliuretano no cortado y cortado preparado de acuerdo con este Ejemplo comparativo. 35 Table 4 - Mechanical properties obtained from stress-strain curves of uncut and cut polyurethane prepared in accordance with this Comparative Example.
- Propiedad Property
- Antes del corte Después del corte Before cutting After cutting
- Límite elástico (MPa) Resistencia en tracción (MPa) Elongación a la rotura (%) Elastic limit (MPa) Tensile strength (MPa) Elongation at break (%)
- 5,3 15,1 766 0,4 0,5 3 5.3 15.1 766 0.4 0.5 3
Ejemplo comparativo 5 Comparative Example 5
40 Se obtuvo un elastómero de poliuretano por reacción de un poliisocianato (Suprasec® 2445 comercial, Huntsman), poliadipato de 1,4-butanodiol (Pm = 1000 Da) (poliéster comercial HOOPOL F523, Synthesia International, Barcelona, España) y 1,4-butanodiol ( Sigma Aldrich, Barcelona, España) como extensor de cadena. Se utilizó una relación NCO/OH de 1,1. 40 A polyurethane elastomer was obtained by reacting a polyisocyanate (commercial Suprasec® 2445, Huntsman), 1,4-butanediol polyadipate (Pm = 1000 Da) (commercial polyester HOOPOL F523, Synthesia International, Barcelona, Spain) and 1, 4-butanediol (Sigma Aldrich, Barcelona, Spain) as a chain extender. An NCO / OH ratio of 1.1 was used.
45 Las propiedades mecánicas del poliuretano se midieron mediante una prueba de esfuerzo-deformación en una máquina de ensayo Instron 4411 Universal aplicándola a diferentes muestras de poliuretano troqueladas en forma de pesa de tipo 2 de acuerdo con la norma ISO 37. La velocidad de tracción fue de 50 mm/min. 45 The mechanical properties of the polyurethane were measured by a stress-strain test in an Instron 4411 Universal test machine by applying it to different samples of die-cut polyurethane type 2 in accordance with ISO 37. The traction speed was 50 mm / min
La autorreparación del elastómero de poliuretano se probó cortando la muestra de prueba con forma de pesa por la The self-repair of the polyurethane elastomer was tested by cutting the test sample in the form of a weight by
50 mitad y volviendo a unir las dos piezas recién cortadas inmediatamente después del corte, en el sitio del corte, y dejándola a 40 °C durante 24 horas Posteriormente, se repitió la prueba de esfuerzo-deformación y se compararon las propiedades mecánicas. 50 half and joining the two newly cut pieces immediately after cutting, at the cutting site, and leaving it at 40 ° C for 24 hours. Subsequently, the stress-strain test was repeated and the mechanical properties were compared.
La Figura 8 muestra el poliuretano con el corte en el medio después de volver a unir, antes y después de la prueba Figure 8 shows the polyurethane with the cut in the middle after reassembly, before and after the test
55 de esfuerzo-deformación. Después de la prueba de esfuerzo-deformación, el poliuretano no se alargó y se rompió en el mismo lugar donde se produjo el corte. Cuando se usa poliéster como poliol, no hay autorreparación del material de poliuretano. 55 stress-strain. After the stress-strain test, the polyurethane did not lengthen and broke in the same place where the cut occurred. When polyester is used as a polyol, there is no self-repair of the polyurethane material.
9 9
La Figura 9 compara las curvas de esfuerzo-deformación del material de poliuretano antes y después de que se produjo el corte. El límite elástico, la resistencia en tracción y el alargamiento a la rotura del poliuretano antes y después del corte se comparan en la Tabla 5. Después de que se produjo el corte, el poliuretano se rompió justo después del comienzo de la prueba de esfuerzo-deformación. Por lo tanto, no hay autorreparación del poliuretano preparado con poliéster como el poliol. Figure 9 compares the stress-strain curves of the polyurethane material before and after the cut occurred. The elastic limit, tensile strength and elongation at breakage of the polyurethane before and after the cut are compared in Table 5. After the cut occurred, the polyurethane broke just after the beginning of the stress test. deformation. Therefore, there is no self-repair of polyurethane prepared with polyester such as polyol.
Tabla 5 -Propiedades mecánicas obtenidas de las curvas de esfuerzo-deformación del poliuretano no cortado y cortado preparado de acuerdo con este Ejemplo comparativo. Table 5 - Mechanical properties obtained from stress-strain curves of uncut and cut polyurethane prepared in accordance with this Comparative Example.
- Propiedad Property
- Antes del corte Después del corte Before cutting After cutting
- Límite elástico (MPa) Resistencia en tracción (MPa) Elongación a la rotura (%) Elastic limit (MPa) Tensile strength (MPa) Elongation at break (%)
- 2,9 2,9 30 0,2 0,2 3 2.9 2.9 30 0.2 0.2 3
10 La Tabla 6 compara las propiedades mecánicas de los materiales de poliuretano como un porcentaje de variación. La autorreparación se produce cuando se obtienen valores del 100 %. Los valores en la Tabla 6 muestran autorreparación en todos los poliuretanos preparados con una mezcla que contiene policarbonato diol. Debido a la alta polaridad del grupo carbonato en comparación con los grupos éster o lactona, las interacciones entre el uretano y el carbonato por enlaces de hidrógeno se verán favorecidas y podrían ser responsables del comportamiento de 10 Table 6 compares the mechanical properties of polyurethane materials as a percentage of variation. Self-repair occurs when 100% values are obtained. The values in Table 6 show self-repair in all polyurethanes prepared with a mixture containing polycarbonate diol. Due to the high polarity of the carbonate group compared to the ester or lactone groups, interactions between urethane and hydrogen carbonate will be favored and could be responsible for the behavior of
15 autorreparación. 15 self-repair.
Tabla 6 -Resumen de eficiencias de autorreparación de los Ejemplos. Table 6 - Summary of self-repair efficiencies of the Examples.
- Ejemplo Example
- Eficiencia de autorreparación (%) Self-repair efficiency (%)
- Límite elástico Elastic limit
- Resistencia en tracción Elongación a la rotura Tensile strength Elongation at break
- 1 one
- 96 84 107 96 84 107
- 2 2
- 202 125 118 202 125 118
- 3 3
- 99 99
- Comp. 4 Comp. 4
- 8 3 0 8 3 0
- Comp. 5 Comp. 5
- 8 8 9 8 8 9
10 10
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15171511.7A EP3103846B1 (en) | 2015-06-10 | 2015-06-10 | Self-healing polyurethane polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2664381T3 true ES2664381T3 (en) | 2018-04-19 |
Family
ID=53498777
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES15171511.7T Active ES2664381T3 (en) | 2015-06-10 | 2015-06-10 | Self-healing polyurethane polymers |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP3103846B1 (en) |
| ES (1) | ES2664381T3 (en) |
| WO (1) | WO2016198441A1 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106832140A (en) * | 2017-01-19 | 2017-06-13 | 中国科学院大学 | A kind of preparation method of multiple selfreparing polyurethane comixing material |
| CN110312756A (en) * | 2017-02-07 | 2019-10-08 | 雷普索尔有限公司 | The purposes of selfreparing poly- (alkylene carbonate) |
| WO2020136599A1 (en) * | 2018-12-28 | 2020-07-02 | Ptt Global Chemical Public Company Limited | A chain extender and a process for preparing a self-healing polyurethane and polyurethane thereof |
| CN112745471B (en) * | 2020-12-29 | 2022-08-09 | 南京理工大学 | Room-temperature intrinsic self-repairing glassy polymer material and preparation method thereof |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1097504A (en) | 1965-03-09 | 1968-01-03 | Upjohn Co | Elastomeric polyurethanes |
| DE1694136B2 (en) | 1967-02-28 | 1974-11-21 | Bayer Ag, 5090 Leverkusen | Process for the production of hydrolysis-resistant polyurethanes |
| GB1202667A (en) | 1968-04-08 | 1970-08-19 | Takeda Chemical Industries Ltd | A method for preparing a polyurethane elastomer solution |
| US4105641A (en) | 1975-05-27 | 1978-08-08 | Bayer Aktiengesellschaft | Process for the preparation of aliphatic polycarbonates and polyurethanes therefrom |
| JPS61179733A (en) | 1985-02-05 | 1986-08-12 | 旭硝子株式会社 | Laminate and manufacture thereof |
| DE69619085T2 (en) * | 1995-12-28 | 2002-06-20 | Asahi Glass Co Ltd | Cross-linked polyurethane sheet and composite made from it |
| US7872078B2 (en) * | 2007-08-28 | 2011-01-18 | Ppg Industries Ohio, Inc. | Curable film-forming compositions demonstrating self-healing properties |
| US7998529B2 (en) * | 2007-10-10 | 2011-08-16 | Ppg Industries Ohio, Inc. | Methods for making polymeric substrates comprising a haze-free, self-healing coating and coated substrates made thereby |
| US8846801B1 (en) * | 2010-02-17 | 2014-09-30 | University Of South Florida | Self-healing polycarbonate containing polyurethane nanotube composite |
| CN103958199B (en) | 2011-12-21 | 2016-08-17 | 东丽株式会社 | Stack membrane |
| US8993066B2 (en) | 2012-02-01 | 2015-03-31 | Nanyang Technological University | Microencapsulation of reactive diisocyanates and the application to self-healing anticorrosion coatings |
| US20140037964A1 (en) | 2012-08-02 | 2014-02-06 | Haipeng Zheng | Optical Article Containing A Self-Healing Coating And Improved Initial Haze |
| KR101587190B1 (en) | 2013-03-15 | 2016-01-20 | 주식회사 엘지화학 | Plastic film |
| JP6220600B2 (en) | 2013-08-22 | 2017-10-25 | 株式会社トクシキ | Silicone part-containing urethane (meth) acrylate copolymer, composition and cured product thereof |
| US10094953B2 (en) * | 2013-09-03 | 2018-10-09 | Essilor International (Compagnie Generale D'optique) | Self-healing hard coatings |
-
2015
- 2015-06-10 EP EP15171511.7A patent/EP3103846B1/en not_active Revoked
- 2015-06-10 ES ES15171511.7T patent/ES2664381T3/en active Active
-
2016
- 2016-06-08 WO PCT/EP2016/063010 patent/WO2016198441A1/en active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| EP3103846B1 (en) | 2018-01-31 |
| EP3103846A1 (en) | 2016-12-14 |
| WO2016198441A1 (en) | 2016-12-15 |
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